Enantiopure Chiral Phosphines Bearing a Sulfinyl Group and their Application in Catalytic Enantiodivergent Synthesis of Polysubstituted Pyrrolines,Advanced Synthesis & Catalysis

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Enantiopure Chiral Phosphines Bearing a Sulfinyl Group and their Application in Catalytic Enantiodivergent Synthesis of Polysubstituted Pyrrolines
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-03-30 , DOI: 10.1002/adsc.202000105
Hanyuan Li ₁ , Bojuan Li ₁ , Jianwei Zeng ₁ , Changzun Jiang ₁ , Zhengjie He _{1,

2}

Affiliation

In this work, a type of enantiopure chiral phosphines bearing a polar S=O sulfinyl group as the chiral unit in the molecule has been developed, which can be prepared in either enantiomeric form from commercially available materials by a three‐step route. The enantiopure chiral phosphines can catalyse enantiodivergent asymmetric [4+1] annulation reactions of α,β‐unsaturated imines and allylic carbonates, delivering polysubstituted pyrrolines in either enantiomeric form in up to 99% yield and up to 99% ee, and thus empower a method for dual stereo‐controlled synthesis of chiral pyrrolines. This work accordingly unveils a practical and predictable strategy to realize enantiodivergent synthesis.

中文翻译：

带有亚磺酰基的对映体纯手性膦及其在多取代吡咯啉催化对映异构合成中的应用

在这项工作中，已开发出一种在分子中带有极性S = O亚磺酰基作为手性单元的对映体纯手性膦，可以通过三步路线从市售材料中以对映体形式制备。对映纯手性膦可以催化α，β-不饱和亚胺和烯丙基碳酸酯的对映体不对称[4 + 1]环化反应，以对映体形式提供多取代的吡咯啉，产率高达99％，ee高达99％。手性吡咯啉的双立体控制合成方法。因此，这项工作揭示了实现对映异构合成的实用且可预测的策略。

更新日期：2020-03-30

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